EP0707794B1 - Disinfectant composition - Google Patents

Disinfectant composition Download PDF

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Publication number
EP0707794B1
EP0707794B1 EP95307484A EP95307484A EP0707794B1 EP 0707794 B1 EP0707794 B1 EP 0707794B1 EP 95307484 A EP95307484 A EP 95307484A EP 95307484 A EP95307484 A EP 95307484A EP 0707794 B1 EP0707794 B1 EP 0707794B1
Authority
EP
European Patent Office
Prior art keywords
chlorhexidine
ethyl alcohol
acid
stability
disinfectant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP95307484A
Other languages
German (de)
French (fr)
Other versions
EP0707794A1 (en
Inventor
Yasuo c/o Shiseido Research Center Igarashi (2)
Takashi c/o Shiseido Research Center Suzuki (2)
Tomoko c/o Shiseido Research Center Kimura (2)
Akira c/o Shiseido Research Center Motoyama (2)
Rina c/o Shiseido Research Center Fukuhara (2)
Atsuko c/o Shiseido Research Center Torii (2)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shiseido Co Ltd
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Shiseido Co Ltd
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Filing date
Publication date
Application filed by Shiseido Co Ltd filed Critical Shiseido Co Ltd
Publication of EP0707794A1 publication Critical patent/EP0707794A1/en
Application granted granted Critical
Publication of EP0707794B1 publication Critical patent/EP0707794B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof

Definitions

  • the present invention relates to a disinfectant composition and, in particular, to stabilization of chlorhexidine in an ethyl alcohol base.
  • Chlorhexidine i.e. 1,1-hexamethylenebis[5-(4-chlorophenyl)biguanide]
  • Chlorhexidine has broad disinfecting action.
  • it has been compounded as a germicidal prophylactic agent for diseases, as an antiseptic, a deodorant, an anti-inflammatory agent in drugs for pyorrhea, and as a disinfectant.
  • the ethanol content in such a mixture is at the same level as that in disinfectant ethanol.
  • US-A-5334388 discloses antimicrobial towels impregnated with compositions containing an antimicrobial agent such as a biguanide, a volatile liquid such as ethanol, an acidity regulator such as citric or lactic acid such that the pH is preferably about 5, and water.
  • an antimicrobial agent such as a biguanide
  • a volatile liquid such as ethanol
  • an acidity regulator such as citric or lactic acid
  • the pH of the compositions for application to the towels is preferably between 4.5 and 7.5, thus rather neutral than acidic.
  • EP-A-0375827 discloses liquid compositions used in the disinfection of skin which contain chlorhexidine, over 50% of ethanol, and an emollient.
  • a liquid composition comprises an organic acid, chlorhexidine and at least 50% by weight ethyl alcohol, and has a pH from 3 to below 4.5. This can be used for disinfecting hands.
  • the organic acid has 2 to 16 carbon atoms.
  • Such organic acids include acetic acid, lactic acid, maleic acid, malic acid, citric acid, salicylic acid, myristic acid, and palmitic acid.
  • lactic acid and citric acid are particularly preferred.
  • glycyrrhizinic acid and its derivatives drugs such as vitamin E, vitamin E acetate, and vitamin B6, and watersoluble polymers such as xanthan gum, dextrin, hydroxyethyl cellulose, hydroxymethyl cellulose, methyl cellulose, carrageenan, and carboxymethyl cellulose, may be compounded.
  • nonionic surfactants and, in order to increase skin-protecting power, urea or the like may be compounded so as to impart a cleaning effect to the composition.
  • Figure 1 is a graph of the relationship between the amount of chlorhexidine remaining, against pH, in lactic acid (o) and citric acid (•) systems.
  • aqueous solutions with the ethyl alcohol concentrations listed below and a chlorhexidine content of 0.2% W/V were prepared and then stored for one month each at 50°C and 0°C. Thereafter, chlorhexidine therein was quantitatively determined. The remaining ratio is calculated as the ratio of the amount of chlorhexidine remaining at 50°C with respect to that at 0°C which is taken as 100%.
  • the concentration thereof should be not lower than 50% by weight or, more preferably, not lower than 70% by weight.
  • the concentration of ethyl alcohol in the mixture was 80% V/V, while each additive was added thereto so as to attain a content of 0.1% W/V.
  • the stability of chlorhexidine in the resulting mixture was evaluated in the same manner as noted above.
  • organic acids having a carbon number from 2 to 16 such as citric acid and lactic acid had a remarkably high stability- imparting action.
  • citric acid, lactic acid, and the like are preferable as compounds which can adjust, with a small amount thereof being added, the pH of the solution having an ethyl alcohol concentration of not lower than 50% by weight from 3 to 5.
  • Hibitane gluconate liquid (with 20% chlorhexidine) 1.0 g Cationic surfactant 0.02 Glyceryl triisooctanate 0.4 Citric acid 0.1 Purified water 18.0 Ethanol q.s. to make 100 ml
  • Hibitane gluconate liquid (with 20% chlorhexidine) 1.0 g Cationic surfactant 0.02 Glyceryl triisooctanate 0.4 Lactic acid 0.1 Purified water 18.0 Ethanol q.s. to make 100 ml
  • chlorhexidine can be compounded therein very stably even when the ethyl alcohol concentration therein is not lower than 50% by weight, thereby satisfying the germicidal property and quick- dryness of the disinfectant.

Description

    Field of the Invention
  • The present invention relates to a disinfectant composition and, in particular, to stabilization of chlorhexidine in an ethyl alcohol base.
    • Background of the Invention
  • Chlorhexidine, i.e. 1,1-hexamethylenebis[5-(4-chlorophenyl)biguanide], has broad disinfecting action. For example, it has been compounded as a germicidal prophylactic agent for diseases, as an antiseptic, a deodorant, an anti-inflammatory agent in drugs for pyorrhea, and as a disinfectant.
  • As infections within a hospital have often been reported recently, the demand for compounds such as chlorhexidine which can be used broadly for disinfection, is expected to increase.
  • It has been reported that, within hospitals, an infection is transferred from one patient to another by doctors and nurses. Accordingly, it is necessary for them to disinfect their hands completely and rapidly after treating or taking care of one patient before treating or taking care of another.
  • Therefore, various quick-drying disinfectants, mainly composed of ethyl alcohol, have recently been studied. Ethyl alcohol alone is insufficient to disinfect hands. Accordingly, chlorhexidine may be added to ethyl alcohol. However, while chlorhexidine is stable in aqueous solution, its stability is low in ethyl alcohol bases.
  • In order to provide quick-drying and germicidal power, it is preferable for the ethanol content in such a mixture to be at the same level as that in disinfectant ethanol. Although there is a demand for disinfectants in which chlorhexidine is stably compounded while maintaining the germicidal property and quick-drying, no product has been found sufficiently satisfactory.
  • US-A-5334388 discloses antimicrobial towels impregnated with compositions containing an antimicrobial agent such as a biguanide, a volatile liquid such as ethanol, an acidity regulator such as citric or lactic acid such that the pH is preferably about 5, and water. This formulation is intended for application to a towel from which the ethanol evaporates, leaving a dry towel. The pH of the compositions for application to the towels is preferably between 4.5 and 7.5, thus rather neutral than acidic.
  • EP-A-0375827 discloses liquid compositions used in the disinfection of skin which contain chlorhexidine, over 50% of ethanol, and an emollient.
    • Summary of the Invention
  • It has now been found that chlorhexidine can stably be compounded in a highly concentrated ethyl alcohol solution when an organic acid is added thereto. According to the present invention, a liquid composition comprises an organic acid, chlorhexidine and at least 50% by weight ethyl alcohol, and has a pH from 3 to below 4.5. This can be used for disinfecting hands.
    • Description of the Invention
  • Preferably, the organic acid has 2 to 16 carbon atoms. Such organic acids include acetic acid, lactic acid, maleic acid, malic acid, citric acid, salicylic acid, myristic acid, and palmitic acid. Among them, lactic acid and citric acid are particularly preferred.
  • Also, other ingredients may be compounded in the disinfectant composition in accordance with the present invention. For example, glycyrrhizinic acid and its derivatives, drugs such as vitamin E, vitamin E acetate, and vitamin B6, and watersoluble polymers such as xanthan gum, dextrin, hydroxyethyl cellulose, hydroxymethyl cellulose, methyl cellulose, carrageenan, and carboxymethyl cellulose, may be compounded.
  • Further, nonionic surfactants and, in order to increase skin-protecting power, urea or the like may be compounded so as to impart a cleaning effect to the composition.
    • The Drawing
  • Figure 1 is a graph of the relationship between the amount of chlorhexidine remaining, against pH, in lactic acid (o) and citric acid (•) systems.
    • Examples
  • In the following, preferable examples of the present invention will be explained. However, the present invention is not restricted to these examples.
    • Stability of Chlorhexidine vs. Ethyl Alcohol Concentration
  • First, the inventors studied the relationship between ethyl alcohol concentration and stability of chlorhexidine.
  • The aqueous solutions with the ethyl alcohol concentrations listed below and a chlorhexidine content of 0.2% W/V were prepared and then stored for one month each at 50°C and 0°C. Thereafter, chlorhexidine therein was quantitatively determined. The remaining ratio is calculated as the ratio of the amount of chlorhexidine remaining at 50°C with respect to that at 0°C which is taken as 100%.
  • The results are shown in TABLE 1.
    Ethyl alcohol conc. 0 10 20 30 40 50 60 70 80
    Remaining ratio 100 95 81 75 69 65 58 53 48
  • On the other hand, when quick- dryness and germicidal power are expected to be improved by ethyl alcohol, the concentration thereof should be not lower than 50% by weight or, more preferably, not lower than 70% by weight.
  • Accordingly, the inventors studied how to improve the stability of chlorhexidine in highly concentrated ethyl alcohol.
    • Stability vs. Various Additives
  • In order to stabilize chlorhexidine in ethyl alcohol, the inventors added various materials, which hardly affected human bodies, to a mixture of chlorhexidine and ethyl alcohol.
  • The concentration of ethyl alcohol in the mixture was 80% V/V, while each additive was added thereto so as to attain a content of 0.1% W/V. The stability of chlorhexidine in the resulting mixture was evaluated in the same manner as noted above.
  • The results are shown in TABLE 2.
    Additive Remaining ratio
    Allantoin 92%
    Glycine 91%
    Citric acid 99%
    Lactic acid 99%
    Butyl hydroxy toluene 91%
    Tocopherol 94%
  • As shown in TABLE 2, it was found that, among various additives, organic acids having a carbon number from 2 to 16 such as citric acid and lactic acid had a remarkably high stability- imparting action.
    • Stability vs. System pH Changed by Addition of Organic Acid
  • Next, in a system having an ethyl alcohol concentration of 80% by weight, the stability of chlorhexidine was evaluated while the pH of the system was changed by the amount of organic acids being added thereto. The stability was evaluated in the same manner as noted above. Since it was difficult to directly determine the pH in a highly concentrated alcohol system, purified water, which had once been boiled and cooled, was added to 5 g of the sample liquid to yield a solution having a whole amount of 50 g. While thus obtained solution was stirred at room temperature, the pH thereof was determined.
  • The results are shown in Fig. 1.
  • As clearly shown in this drawing, advantageous effects were recognized at the region where pH was from 3 to 5. In particular, the optimum region for stabilizing chlorhexidine existed near a pH of 4.
  • As a result, it is understood that citric acid, lactic acid, and the like, as noted above, are preferable as compounds which can adjust, with a small amount thereof being added, the pH of the solution having an ethyl alcohol concentration of not lower than 50% by weight from 3 to 5.
  • In the following, more specific compounding examples of disinfectant compositions in which chlorhexidine was stably compounded will be described.
    • COMPOUNDING EXAMPLE 1
  • Hibitane gluconate liquid (with 20% chlorhexidine) 1.0 g
    Cationic surfactant 0.02
    Glyceryl triisooctanate 0.4
    Citric acid 0.1
    Purified water 18.0
    Ethanol q.s. to make 100 ml
    • COMPOUNDING EXAMPLE 2
  • Hibitane gluconate liquid (with 20% chlorhexidine) 1.0 g
    Cationic surfactant 0.02
    Glyceryl triisooctanate 0.4
    Lactic acid 0.1
    Purified water 18.0
    Ethanol q.s. to make 100 ml
  • Both disinfectant compositions in accordance with these compounding examples exhibited an excellent stability.
  • As explained in the foregoing, in the disinfectant composition in accordance with the present invention, as an organic acid is added thereto, chlorhexidine can be compounded therein very stably even when the ethyl alcohol concentration therein is not lower than 50% by weight, thereby satisfying the germicidal property and quick- dryness of the disinfectant.

Claims (4)

  1. A liquid composition comprising an organic acid, chlorhexidine and at least 50% by weight ethyl alcohol, and having a pH from 3 to below 4.5.
  2. A composition according to claim 1, wherein the organic acid has 2 to 16 carbon atoms.
  3. A composition according to claim 2, wherein the organic acid is lactic acid or citric acid.
  4. Use of a composition according to any of claims 1 to 3, for disinfecting hands.
EP95307484A 1994-10-21 1995-10-20 Disinfectant composition Expired - Lifetime EP0707794B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP282976/94 1994-10-21
JP28297694 1994-10-21
JP28297694A JP3515821B2 (en) 1994-10-21 1994-10-21 Disinfecting composition

Publications (2)

Publication Number Publication Date
EP0707794A1 EP0707794A1 (en) 1996-04-24
EP0707794B1 true EP0707794B1 (en) 2001-04-11

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Application Number Title Priority Date Filing Date
EP95307484A Expired - Lifetime EP0707794B1 (en) 1994-10-21 1995-10-20 Disinfectant composition

Country Status (6)

Country Link
US (1) US5800827A (en)
EP (1) EP0707794B1 (en)
JP (1) JP3515821B2 (en)
KR (2) KR100414599B1 (en)
AU (1) AU694264B2 (en)
DE (1) DE69520639T2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8034844B2 (en) 2006-05-30 2011-10-11 The Dial Corporation Compositions having a high antiviral efficacy
US8337872B2 (en) 2006-06-02 2012-12-25 The Dial Corporation Method of inhibiting the transmission of influenza virus

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19713850A1 (en) * 1997-04-04 1998-10-08 Henkel Ecolab Gmbh & Co Ohg Disinfection procedure (II)
JP3636611B2 (en) * 1999-03-19 2005-04-06 日華化学株式会社 Disinfectant composition
US6899897B2 (en) 2001-06-18 2005-05-31 Jaleva, Inc. Gum resin as a carrier for topical application of pharmacologically active agents
US7338927B2 (en) * 2002-08-20 2008-03-04 Alda Pharmaceuticals Corp. Wide spectrum disinfectant comprising an alcohol and disinfectant mixture
US9028852B2 (en) * 2004-09-07 2015-05-12 3M Innovative Properties Company Cationic antiseptic compositions and methods of use
US20060074029A1 (en) * 2004-10-04 2006-04-06 Scott Leece Topical antimicrobial composition having improved moisturization properties
US20080267904A1 (en) * 2004-12-09 2008-10-30 The Dial Corporation Compositions Having A High Antiviral And Antibacterial Efficacy
MX2007006864A (en) * 2004-12-09 2008-02-15 Dial Corp Compositions having a high antiviral and antibacterial efficacy.
JP2008523064A (en) * 2004-12-09 2008-07-03 ザ ダイアル コーポレイション Composition with excellent antiviral and antibacterial activity
DE602005023901D1 (en) * 2004-12-09 2010-11-11 Dial Corp COMPOSITIONS HAVING HIGH ANTIVIRAL AND ANTIBACTERIAL EFFECT
US20090012174A1 (en) * 2004-12-09 2009-01-08 The Dial Corporation Compositions Having a High Antiviral and Antibacterial Efficacy
MX2007006863A (en) * 2004-12-09 2008-02-25 Dial Corp Compositions having a high antiviral and antibacterial efficacy.
US20080317690A1 (en) * 2005-11-07 2008-12-25 Alex Battaglia Film-Forming Resins as a Carrier for Topical Application of Pharmacologically Active Agents
US20070175972A1 (en) * 2005-11-10 2007-08-02 Ringer Eric M Manually actuated contactless card
US8119115B2 (en) 2006-02-09 2012-02-21 Gojo Industries, Inc. Antiviral method
US8450378B2 (en) 2006-02-09 2013-05-28 Gojo Industries, Inc. Antiviral method
US9629361B2 (en) 2006-02-09 2017-04-25 Gojo Industries, Inc. Composition and method for pre-surgical skin disinfection
EP2040543A2 (en) * 2006-05-24 2009-04-01 The Dial Corporation Composition and method for controlling the transmission of noroviruses
US20070274926A1 (en) * 2006-05-26 2007-11-29 The Dial Corporation Method of inhibiting the transmission of viruses
RU2008152101A (en) * 2006-05-31 2010-07-10 Дзе Дайл Корпорейшн (Us) Alcohol-Containing Antimicrobial Compositions with Increased Efficiency
RU2008152442A (en) * 2006-06-05 2010-07-20 Дзей Дайл Корпорейшн (Us) METHODS AND PRODUCTS HAVING HIGH ANTIVIRAL AND ANTI-BACTERIAL EFFICIENCY
DE102009009517A1 (en) 2009-02-18 2010-08-19 Sprick Gmbh Bielefelder Papier- Und Wellpappenwerke & Co. Drive mechanism for a device for laying a fiber material web in a Leporellofaltung
ES2569085T3 (en) * 2009-11-24 2016-05-06 Fresenius Medical Care Deutschland Gmbh Disinfectant composition
EP3102661B1 (en) 2014-02-07 2020-08-05 GOJO Industries, Inc. Compositions and methods with efficacy against spores and other organisms
US9578879B1 (en) 2014-02-07 2017-02-28 Gojo Industries, Inc. Compositions and methods having improved efficacy against spores and other organisms
CN104622852B (en) * 2015-02-10 2017-08-25 山东天达有限公司 A kind of polysaccharide-modified ethanol water and its preparation method and application
US10813357B1 (en) * 2015-05-26 2020-10-27 Gojo Industries, Inc. Compositions and methods with efficacy against spores and other organisms
DE102015122276A1 (en) 2015-12-18 2017-06-22 Schülke & Mayr GmbH Alcoholic compositions containing octenidine dihydrochloride
DE102015122263A1 (en) 2015-12-18 2017-06-22 Schülke & Mayr GmbH Alcoholic disinfectant for the control of viruses
CO2018009513A2 (en) 2016-02-12 2018-09-20 Salicylates & Chemicals Pvt Ltd Synthesis and application of new antimicrobial assets
US10813892B2 (en) * 2016-05-24 2020-10-27 Carefusion 2200, Inc. Antiseptic solutions and applicators
EP3849313A1 (en) * 2018-09-14 2021-07-21 3M Innovative Properties Company Antimicrobial compositions comprising chlorhexidine
KR102267156B1 (en) 2020-12-23 2021-06-21 주식회사 비바케어 (Composition for sterilization or disinfection and manufacturing method thereof
CN116530515A (en) * 2022-01-26 2023-08-04 上海交通大学 Disinfection product based on citric acid and natural naphthoquinone compounds

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985001876A1 (en) * 1983-10-24 1985-05-09 Lockley Services Pty. Ltd. Foamable biocide composition
DE3542516A1 (en) * 1985-12-02 1987-06-04 Henkel Kgaa DISINFECTANT
GB8604986D0 (en) * 1986-02-28 1986-04-09 Unilever Plc Disinfectant compositions
DE3702983A1 (en) * 1986-06-09 1987-12-10 Henkel Kgaa DISINFECTANT AND THEIR USE FOR SKIN AND MUCUS SKIN DISINFECTION
DE3743374A1 (en) * 1987-12-21 1989-06-29 Henkel Kgaa USE OF BISGUANIDE-CONTAINING COMPOSITIONS AGAINST EGGS OF THE MEGEWORM
DE3809980C2 (en) * 1988-03-24 1998-02-19 Stankiewicz Gmbh Structure for sound insulation, process for its production and its use
JPH02140167A (en) * 1988-11-22 1990-05-29 Saraya Kk Composition for disinfecting hand and finger
US5004757A (en) * 1988-12-20 1991-04-02 Wave Energy Systems, Inc. Virucidal low toxicity compositions
JPH03215411A (en) * 1989-09-14 1991-09-20 Kanebo Ltd Mouth washing solution
US5167950A (en) * 1991-03-28 1992-12-01 S. C. Johnson & Son High alcohol content aerosol antimicrobial mousse
KR940010078A (en) * 1992-10-06 1994-05-24 윤종용 How to switch to the main screen during multi-screen recording
US5334388A (en) * 1993-09-15 1994-08-02 Becton, Dickinson And Company Antimicrobial drying substrate
WO1995012395A1 (en) * 1993-11-05 1995-05-11 E.R. Squibb And Sons, Inc. Topical antimicrobial cleanser containing chlorhexidine gluconate and alcohol

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8034844B2 (en) 2006-05-30 2011-10-11 The Dial Corporation Compositions having a high antiviral efficacy
US8337872B2 (en) 2006-06-02 2012-12-25 The Dial Corporation Method of inhibiting the transmission of influenza virus

Also Published As

Publication number Publication date
KR100414599B1 (en) 2004-03-06
KR100437566B1 (en) 2004-06-30
EP0707794A1 (en) 1996-04-24
AU3439895A (en) 1996-05-02
JP3515821B2 (en) 2004-04-05
KR960013197A (en) 1996-05-22
JPH08119811A (en) 1996-05-14
DE69520639D1 (en) 2001-05-17
US5800827A (en) 1998-09-01
AU694264B2 (en) 1998-07-16
DE69520639T2 (en) 2001-08-02

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